That idea was indeed a “nugget” in my presentation–something I mentioned briefly without elaborating. In my own trial preparation practice, I don’t uniformly ask clients this question. My colleague’s comment has me realizing that I should start.

In any attorney-client relationship one of the most difficult tasks is overcoming the client’s embarrassment to disclose information that could prevent that client from achieving his or her goals. Folks are naturally reluctant to discuss what shames them, but overcoming this reluctance if vital to understanding the weaknesses of a client’s case. Almost every attorney has a “war story” about a case that fell apart when the client was asked a question on cross examination that revealed information of which the attorney was completely ignorant. Asking the client during trial preparation what question(s) he or she dreads reduces the possibility of such shocks.

Assuming the client answers that question untruthfully, and the trial goes poorly when that client is asked a case-destroying question that the attorney and client are completely unprepared for, the attorney can note this inaccurate answer if the client indulges the post-trial blame game. However, assuming the client answers this question truthfully, that response can prompt two effective actions. First, if the information is so damaging that the client is unlikely to achieve his or her goals if the question is asked, this is a signal that goals need to be reduced and settlement options need to be pursued more vigorously.

More likely, the answer to this question will be something damaging but not fatal. The task then is to rehearse the answer. The goal is to answer the question truthfully and forthrightly but to limit the damage. If the answer is merely embarrassing, or involves some distant action of limited relevance, a short answer that does not include context should be sufficient. In these circumstances providing additional context may only serve to highlight unfavorable information. If the answer would disturb the fact finder, more explanation may be required. Here, the task for the attorney and client is to develop that explanation. “It was not my best moment” or ‘it was not a moment I am proud of,” followed by an explanation of what the client learned from it can humanize the client and turn a negative into something that contains some small positive element.

There are some attorneys who try to win trials by ambush: ask the opposing party embarrassing questions and watch them lie and fluster. By preparing the client for such questions, one prevents opposing counsel from successfully employing this strategy. There is a tremendous satisfaction in watching opposing counsels’ faces when they ask such “gotcha” questions and get responses that actually help one’s client.